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Merck
CN

G4705

L-Glutathione reduced

98%

Synonym(s):

γ-L-Glutamyl-L-cysteinyl-glycine, GSH

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About This Item

Linear Formula:
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
CAS Number:
70-18-8
Molecular Weight:
307.32
EC Number:
200-725-4
UNSPSC Code:
12352103
MDL number:
MFCD00065939
Beilstein/REAXYS Number:
1729812

Key Documents

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assay

98%

optical activity

[α]25/D −17.0°, c = 2 in H2O

mp

192-195 °C (dec.) (lit.)

SMILES string

N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O

InChI

1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

InChI key

RWSXRVCMGQZWBV-WDSKDSINSA-N

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Application

Biological antioxidant that has been used with antitumor agents to enhance activity or to reduce side effects.
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.

Biochem/physiol Actions

Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Storage Class

13 - Non Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
04431CT
04127HV
06429TT
17204TA
16112CO

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Journal of the American Chemical Society, 116, 6537-6537 (1994)
J H Lee et al.
Cancer research, 54(9), 2398-2403 (1994-05-01)
7-N-((2-([2-(gamma-L-Glutamylamino)ethyl]dithio)ethyl))mitomycin C (KW-2149) is an analogue of mitomycin C (MMC) and has prominent activities against various tumors. We studied the antitumor effects of KW-2149 in MMC-resistant variants of human colon carcinoma HT-29 (HT-29/MMC) and mouse hepatoma Hepa-I (C4, B13NBii1) cells
J. Optim. Nutr., 2, 173-173 (1993)
Mario Faúndez et al.
Antimicrobial agents and chemotherapy, 52(5), 1837-1839 (2008-03-12)
L-buthionine (S,R)-sulfoximine (BSO) at a dose of 220 mg/kg of body weight/day showed an anti-Trypanosoma cruzi effect in infected mice, increasing their survival rate and decreasing the parasitemias and parasite burden in the hearts. Treatment with BSO plus nifurtimox caused
Minakshi C Gurbhele-Tupkar et al.
Bioorganic & medicinal chemistry, 16(5), 2579-2590 (2007-12-11)
Almost all therapeutic proteins and most extracellular proteins contain disulfide bonds. The production of these proteins in bacteria or in vitro is challenging due to the need to form the correctly matched disulfide bonds during folding. One important parameter for
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